CA2082696A1 - Ppe/polyamide compositions of improved melt strength - Google Patents
Ppe/polyamide compositions of improved melt strengthInfo
- Publication number
- CA2082696A1 CA2082696A1 CA002082696A CA2082696A CA2082696A1 CA 2082696 A1 CA2082696 A1 CA 2082696A1 CA 002082696 A CA002082696 A CA 002082696A CA 2082696 A CA2082696 A CA 2082696A CA 2082696 A1 CA2082696 A1 CA 2082696A1
- Authority
- CA
- Canada
- Prior art keywords
- thermoplastic composition
- amine
- polyamide
- acid
- diamine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 75
- 229920002647 polyamide Polymers 0.000 title claims abstract description 51
- 239000004952 Polyamide Substances 0.000 title claims abstract description 50
- 229920000642 polymer Polymers 0.000 claims abstract description 44
- 229920001955 polyphenylene ether Polymers 0.000 claims abstract description 32
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 31
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 31
- 150000001412 amines Chemical class 0.000 claims abstract description 27
- 150000004985 diamines Chemical class 0.000 claims abstract description 16
- 229920000768 polyamine Polymers 0.000 claims abstract description 14
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000155 melt Substances 0.000 claims abstract description 8
- 238000000071 blow moulding Methods 0.000 claims abstract description 7
- -1 poly(2,3,6-trimethyl-1,4-phenylene) Polymers 0.000 claims description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 26
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 14
- 229920001577 copolymer Polymers 0.000 claims description 14
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 229920001400 block copolymer Polymers 0.000 claims description 13
- 239000000178 monomer Substances 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- 229920002554 vinyl polymer Polymers 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000004609 Impact Modifier Substances 0.000 claims description 7
- 235000011037 adipic acid Nutrition 0.000 claims description 7
- 239000001361 adipic acid Substances 0.000 claims description 7
- 150000001993 dienes Chemical class 0.000 claims description 7
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 4
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000008188 pellet Substances 0.000 claims description 4
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 claims description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 claims description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 4
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims description 4
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 2
- GVLZQVREHWQBJN-UHFFFAOYSA-N 3,5-dimethyl-7-oxabicyclo[2.2.1]hepta-1,3,5-triene Chemical compound CC1=C(O2)C(C)=CC2=C1 GVLZQVREHWQBJN-UHFFFAOYSA-N 0.000 claims description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- ZETYUTMSJWMKNQ-UHFFFAOYSA-N n,n',n'-trimethylhexane-1,6-diamine Chemical compound CNCCCCCCN(C)C ZETYUTMSJWMKNQ-UHFFFAOYSA-N 0.000 claims description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 claims 2
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 claims 1
- MRNZSTMRDWRNNR-UHFFFAOYSA-N bis(hexamethylene)triamine Chemical compound NCCCCCCNCCCCCCN MRNZSTMRDWRNNR-UHFFFAOYSA-N 0.000 claims 1
- 238000007664 blowing Methods 0.000 claims 1
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 claims 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 19
- 150000002500 ions Chemical class 0.000 description 10
- 229920002302 Nylon 6,6 Polymers 0.000 description 6
- 229920000265 Polyparaphenylene Polymers 0.000 description 5
- 229920002292 Nylon 6 Polymers 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003607 modifier Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical compound COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-UHFFFAOYSA-N 0.000 description 1
- QAMVRQIZKGCYOX-UHFFFAOYSA-N 2-ethenylnaphthalene-1-carbaldehyde Chemical compound C1=CC=CC2=C(C=O)C(C=C)=CC=C21 QAMVRQIZKGCYOX-UHFFFAOYSA-N 0.000 description 1
- VSKJLJHPAFKHBX-UHFFFAOYSA-N 2-methylbuta-1,3-diene;styrene Chemical class CC(=C)C=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 VSKJLJHPAFKHBX-UHFFFAOYSA-N 0.000 description 1
- FQLAJSQGBDYBAL-UHFFFAOYSA-N 3-(azepane-1-carbonyl)benzamide Chemical compound NC(=O)C1=CC=CC(C(=O)N2CCCCCC2)=C1 FQLAJSQGBDYBAL-UHFFFAOYSA-N 0.000 description 1
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- GVNWZKBFMFUVNX-UHFFFAOYSA-N Adipamide Chemical compound NC(=O)CCCCC(N)=O GVNWZKBFMFUVNX-UHFFFAOYSA-N 0.000 description 1
- 102100025991 Betaine-homocysteine S-methyltransferase 1 Human genes 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 101150039033 Eci2 gene Proteins 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 101000933413 Homo sapiens Betaine-homocysteine S-methyltransferase 1 Proteins 0.000 description 1
- 229920006063 Lamide® Polymers 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- 101100400378 Mus musculus Marveld2 gene Proteins 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 101150034459 Parpbp gene Proteins 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- QBPFLULOKWLNNW-UHFFFAOYSA-N chrysazin Chemical compound O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O QBPFLULOKWLNNW-UHFFFAOYSA-N 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- KVFIJIWMDBAGDP-UHFFFAOYSA-N ethylpyrazine Chemical compound CCC1=CN=CC=N1 KVFIJIWMDBAGDP-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002531 isophthalic acids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920013636 polyphenyl ether polymer Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229920006132 styrene block copolymer Polymers 0.000 description 1
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 description 1
- 150000003504 terephthalic acids Chemical class 0.000 description 1
- DJZKNOVUNYPPEE-UHFFFAOYSA-N tetradecane-1,4,11,14-tetracarboxamide Chemical compound NC(=O)CCCC(C(N)=O)CCCCCCC(C(N)=O)CCCC(N)=O DJZKNOVUNYPPEE-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C08L71/12—Polyphenylene oxides
- C08L71/123—Polyphenylene oxides not modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Blow-Moulding Or Thermoforming Of Plastics Or The Like (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81521291A | 1991-12-31 | 1991-12-31 | |
| US815,212 | 1991-12-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2082696A1 true CA2082696A1 (en) | 1993-07-01 |
Family
ID=25217186
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002082696A Abandoned CA2082696A1 (en) | 1991-12-31 | 1992-11-12 | Ppe/polyamide compositions of improved melt strength |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5576387A (enrdf_load_stackoverflow) |
| EP (1) | EP0553556B1 (enrdf_load_stackoverflow) |
| JP (1) | JPH0737569B2 (enrdf_load_stackoverflow) |
| CA (1) | CA2082696A1 (enrdf_load_stackoverflow) |
| DE (1) | DE69218394T2 (enrdf_load_stackoverflow) |
| ES (1) | ES2098462T3 (enrdf_load_stackoverflow) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4414044A1 (de) * | 1994-04-22 | 1995-10-26 | Basf Ag | Polyphenylenether/Polyamid-Formmassen |
| EP0719834A3 (en) * | 1994-12-30 | 1997-01-02 | Gen Electric | Heat resistant compositions containing polyphenylene homopolymers with high glass transition temperature |
| US6107415A (en) * | 1998-09-08 | 2000-08-22 | General Electric Company | Uncompatibilized polyphenylene ether-polyamide compositions |
| FR2812880B1 (fr) * | 2000-08-09 | 2006-06-16 | Rhodia Eng Plastics Srl | Copolyamides et compositions a base de ces copolyamides |
| FR2812879B1 (fr) * | 2000-08-09 | 2002-10-25 | Rhodia Eng Plastics Srl | Copolyamides et compositions a base de ces copolyamides |
| US20060205872A1 (en) * | 2003-08-16 | 2006-09-14 | General Electric Company | Reinforced Poly(Arylene Ether)/Polyamide Composition and Articles Thereof |
| US7439284B2 (en) * | 2004-03-31 | 2008-10-21 | Sabic Innovative Plastics Ip B.V. | Method of making poly(arylene ether) compositions |
| US20080081874A1 (en) * | 2006-09-29 | 2008-04-03 | Kim Balfour | Poly(arylene ether) composition, method, and article |
| US20080081879A1 (en) * | 2006-09-29 | 2008-04-03 | Kim Balfour | Crosslinked block copolymer composition and method |
| US8795557B2 (en) * | 2008-03-31 | 2014-08-05 | Sabic Innovative Plastics Ip B.V. | Flame resistant polyphthalamide/poly(arylene ether) composition |
| US8057873B2 (en) * | 2008-04-28 | 2011-11-15 | Sabic Innovative Plastics Ip B.V. | Injection molded article and method for the manufacture thereof |
| US7790791B2 (en) | 2008-10-21 | 2010-09-07 | Sabic Innovative Plastics Ip B.V. | Injection molded article and method for the manufacture thereof |
| US8524137B2 (en) | 2011-05-26 | 2013-09-03 | Sabic Innovative Plastics Ip B.V. | Injection molded article and method for the manufacture thereof |
| US8865279B2 (en) | 2013-03-04 | 2014-10-21 | Sabic Global Technologies B.V. | Reinforced polyphthalamide/poly(phenylene ether) composition |
| MX2022004816A (es) | 2019-10-24 | 2022-05-16 | Invista Textiles Uk Ltd | Composiciones de poliamida y articulos fabricados a partir de estas. |
| EP4288491A1 (en) | 2021-02-08 | 2023-12-13 | INVISTA Textiles (U.K.) Limited | Blow-moldable polyamide compositions |
| WO2022208319A1 (en) | 2021-03-30 | 2022-10-06 | Inv Nylon Chemicals Americas, Llc | Polyamide composition for forming sheets |
| EP4326821A1 (en) | 2021-04-22 | 2024-02-28 | INVISTA Textiles (U.K.) Limited | Polyamide composition |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3687904A (en) * | 1970-12-04 | 1972-08-29 | Ici Ltd | Polyamides |
| JPS5941663B2 (ja) * | 1979-07-20 | 1984-10-08 | 住友化学工業株式会社 | 樹脂組成物の製造法 |
| US4600741A (en) * | 1984-09-27 | 1986-07-15 | General Electric Company | Polyphenylene ether-polyamide blends |
| US4642358A (en) * | 1984-09-27 | 1987-02-10 | General Electric Company | Acyl modified polyphenylene ether composition |
| JPH07727B2 (ja) * | 1985-11-26 | 1995-01-11 | 三菱油化株式会社 | 樹脂組成物 |
| US4654405A (en) * | 1985-12-05 | 1987-03-31 | Borg-Warner Chemicals, Inc. | Carboxylated phenylene ether resins |
| US4732938A (en) * | 1985-12-06 | 1988-03-22 | Borg-Warner Chemicals, Inc. | Thermoplastic polyamide--polyphenylene ether compositions |
| US4659763A (en) * | 1986-01-06 | 1987-04-21 | General Electric Company | Modified polyphenylene ether-polyamide compositions |
| DE3742444A1 (de) * | 1987-12-15 | 1989-07-06 | Basf Ag | Thermoplastische formmassen |
| US4900786A (en) * | 1988-06-23 | 1990-02-13 | General Electric Company | Polyphenylene ether/rubber modified polystyrene composition suitable for blow molding large parts |
| DE3823803A1 (de) * | 1988-07-14 | 1990-01-18 | Basf Ag | Thermoplastische formmassen auf der basis von polyamidmischungen |
| JP2709110B2 (ja) * | 1988-12-12 | 1998-02-04 | 三菱化学株式会社 | ポリフェニレンエーテル系樹脂組成物 |
| DE3905038A1 (de) * | 1989-02-18 | 1990-08-23 | Basf Ag | Flammgeschuetzte thermoplastische formmassen auf der basis von phlegmatisiertem roten phosphor |
| DE3926904A1 (de) * | 1989-08-16 | 1991-02-21 | Basf Ag | Verfahren zur herstellung von verstaerkten, zaehmodifizierten thermoplastischen formmassen |
-
1992
- 1992-11-12 CA CA002082696A patent/CA2082696A1/en not_active Abandoned
- 1992-12-15 DE DE69218394T patent/DE69218394T2/de not_active Expired - Fee Related
- 1992-12-15 ES ES92311456T patent/ES2098462T3/es not_active Expired - Lifetime
- 1992-12-15 EP EP92311456A patent/EP0553556B1/en not_active Expired - Lifetime
- 1992-12-21 JP JP4356973A patent/JPH0737569B2/ja not_active Expired - Fee Related
-
1993
- 1993-11-12 US US08/152,068 patent/US5576387A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0553556A2 (en) | 1993-08-04 |
| EP0553556A3 (enrdf_load_stackoverflow) | 1994-03-09 |
| EP0553556B1 (en) | 1997-03-19 |
| DE69218394D1 (de) | 1997-04-24 |
| JPH05287194A (ja) | 1993-11-02 |
| JPH0737569B2 (ja) | 1995-04-26 |
| DE69218394T2 (de) | 1997-09-18 |
| US5576387A (en) | 1996-11-19 |
| ES2098462T3 (es) | 1997-05-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |